Skip Navigation

Nucleic Acids Symposium Series 2004 48(1):43-44; doi:10.1093/nass/48.1.43
© 2004 by Oxford University Press
This Article
Right arrow FREE Full Text (PDF) Freely available
Right arrow Alert me when this article is cited
Right arrow Alert me if a correction is posted
Services
Right arrow Email this article to a friend
Right arrow Similar articles in this journal
Right arrow Similar articles in PubMed
Right arrow Alert me to new issues of the journal
Right arrow Add to My Personal Archive
Right arrow Download to citation manager
Right arrowRequest Permissions
Google Scholar
Right arrow Articles by Haraguchi, K.
Right arrow Articles by Tanaka, H.
Right arrow Search for Related Content
PubMed
Right arrow PubMed Citation
Right arrow Articles by Haraguchi, K.
Right arrow Articles by Tanaka, H.
Social Bookmarking
Add to CiteULike   Add to Connotea   Add to Del.icio.us  
What's this?

An alternative method suitable for a large scale synthesis of 4'-ethynyl-2',3'-didehydro-3'-deoxythymidine

Kazuhiro Haraguchi, Masanori Sumino, Shingo Takeda and Hiromichi Tanaka

School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan

Reaction of 4', 5'-unsaturated thymine nucleoside 1 with Pb(OBz)4 gave the 4'-benzoyloxy derivative 9 as a diastereomeric mixture in 79% yield. When 9 was treated with Me3Al in CH2Cl2 at 0 °C, spiro-derivative 10 was formed as the major product in 76% yield. On the other hand, the use of Me2AlCl led to the formation of the 4'-chlorinated product 11, which was subjected to in situ treatment with Me3Al to give the 4'-{alpha}-methyl derivative 12 (15%) as well as the 4'-ß-methyl counterpart 13 (38%). Formation of 11 was also observed during the reaction between 9 and EtAl(Cl)C{equiv}CTMS, prepared from EtAlCl2 and LiC{equiv}CTMS. From this reaction, the 4'-ethynyl nucleoside 14 was obtained stereoselectively in 56% yield.


Add to CiteULike CiteULike   Add to Connotea Connotea   Add to Del.icio.us Del.icio.us    What's this?




Disclaimer:
Please note that abstracts for content published before 1996 were created through digital scanning and may therefore not exactly replicate the text of the original print issues. All efforts have been made to ensure accuracy, but the Publisher will not be held responsible for any remaining inaccuracies. If you require any further clarification, please contact our Customer Services Department.